Anna Nicole Smith

The Texas native dropped out of high school to marry at the age of 17 and give birth to her only son, Daniel, who died of a drug overdose in 2006 at age 20.

A former Guess model, Smith became an American sex symbol in 1992 when she was chosen to appear on the cover of Playboy, which led to a lucrative modeling career and a short-lived reality series. She achieved notoriety in 1994 with her marriage to 90-year-old J. Howard Marshall, who passed away just over a year after the couple said their vows.

Smith famously battled Marshall’s family for control over the oil tycoon’s billions. The widow proceeded to have flings with Frédéric Prinz von Anhalt (Zsa Zsa Gabor’s ninth husband), her former bodyguard, and Mark “Hollywood” Hatten.

In 2007, Smith died suddenly of drug-related causes. A custody battle over her infant daughter Dannielynn, ensued, further cementing Smith’s legacy as a staple of celebrity legal squabbles. Dannielynn’s biological father was determined to be Larry Birkhead, not Smith’s lawyer, Howard K. Stern, as stern vehemently alleged. Smith’s life – seen by many as a story of “famous for being famous” celebrity excess – is the subject of an upcoming biopic starring Willa Ford.